Capillary active compounds and process of preparing them



Patented Aug. 5, 1941 CAPILLARY ACTIVE COMPOUNDS AND PROCESS OFPREPARING THEM Ludwig Orthner, Carl Platz, and HansKeller,Frankfort-on-the-Main, and Heinz Siinke, Bad

Soden in Taunus, Germany,

assignors to I. G.

Farbenindustrie Aktlengeselischaft, Frankforton-the-Main, Germany NoDrawing.-

. No. 250,923. In Germany January 17,

8 Claims.

The present invention relates to capillary active compounds and to aprocess of preparing them.

' Application January 14, 1939, Serial We have found that agents of highcapillary action are obtainable by introducing hydrophiiic groups,directly or indirectly, into an amine of the following general formulaSuch amines are, for instance, di-(n-hexyD- amine, diisohexylamine,di-alpha-ethylhexylamine, di-octylamine. butyldodecylamine,didodecylamine, di-octodecylamine, methyl-dihexylamine,diisoheptyl-hydroxyethyl-amine, diheptyl-benzylamine. Suchsecondaryamines may be I obtained by known methods from carboxylic acids ormixtures of carboxylic acids, for instance, by transforming these acidsinto the nitriles and carbon to react with potassium cyanide andsaponiiying the product obtained.

The amines may also be obtained by other known methods, for instance, bycausing suitable halogenated hydrocarbons to react with ammonia oramines. v

- The method of rendering the products watersoluble consists intransforming the amines, by means of phosgene, into carbamic acidchlorides and then condensing these products with aminoacids, such assarcosine, methyl-taurine, with albumin' decomposition products or withaminopoly-hydroxy-compounds such as methylgluca-' mine orhydroxy-sul'fonic acids, such as hydroxyethane-sulfonic acid.

The products obtained by the process of the invention have capillaryactive properties and may be used for treating materials of variouskind, such as textiles, leather, paper and the like. They display a highwetting and emulsifying action; they may also be used with advantage aslevelling and penetrative dyeing agents. Some hydrogenating the nitrilesthus obtained. Primary amines which are simultaneously formed areseparated by distillation. Suitable carboxylic acids are, for instance,caproic acid, caprylic acid, capric acid, lauric acid, palmitic acid,stearic acid, oleic acid, ricinolic acid, alpha-ethylhexylic acid.Theamlnes may be used as such or in admixture with one another. Theparent materials may also be prepared from commercial mixtures ofcarboxylic acids. It is, for instance, possible to transform intoamines, by way of nitriles, the carboxylic acid mixtures formed in theoxidation of paraflin or of mineral oils. There are further suitable themixtures of carboxylic acids which are obtained by treating with alkalithe alcohols 01 high molecular weight formed in the catalytichydrogenation of carbon oxides.

Parent materials suitable for the preparation of amines are alsocarboxylic acids or mixtures of carboxylic acids which are obtained bytreating carbon monoxide or carbon dioxide, in the presence of anoleflne and perhaps of hydrogen, with steam or by causing a halogenatedhydroof the products have a washing power or may be used as softeningagents. The wetting effect, even in mercerizlng liquors, is especiallyhigh with compounds inwhich the radicals R and R1 contain branchedchains. The products may be used as such, in admixture with one anotheror with other capillary active substances, such as soap and othertextile adjuvants, with colloidal substances such as mucilage, glue,water-soluble cellulose derivatives, starch, bentonite, saponine or thelike or with organic solvents, such as butanol, xylenyl-glycol; but alsowith inorganic salts, such as Glaubers salt, sodium carbonate, sodiumpyrophosphate, trisodium phosphate, sodium metaphosphate or with agentsyielding oxygen such as sodium perborate or sodium hypochlorite.

The following examples serve to illustrate the invention, but they arenot intended to limit it thereto; the parts are by weight:

(1) 213 parts of diisoheptylamine are dissolved in 450 parts ofchlorobenzene and dry hydrochloric acid gas is then introduced, whilecooling, until saturation. The temperature is then raised to C. to C.and phosgene is introduced,

'hvdrochloric acid gas being developed. When the developement ofhydrochloric acid gas has ceased. phosgene and hydrochloric acid gasstill present are removed by the introduction of dry air and the solventis then distilled under reduced ressure. 240 parts ofdiisoheptyl'carbamic acid chloride boiling under a pressure of 2 mm. at140 C. to 142 C. are obtained.

- solution is distinctly alkaline towards 55 parts ofdiisohcptylcarbamic acid chloride of the formula C1111: and caustic sodasolution are added in the course of about hours at 75 C. to 80 C., whilestirring, to 330 parts of a methyl taurine solution of 10 per centstrength so that the reaction of the phenolphthalein. The reactionproduct dissolves in wataurine.

2) Di- (alpha-ethylhexyl) -amine trans- I formed by means of phosgeneinto the carbamic acid chloride having the formula CaHn ' NC0.Cl

CaHn and 30 parts thereof are added, drop by drop, at 75 C. to 85 0.into an aqueous solution-containing 23 parts of sodium n-butyltaurine inthe course of 10 to hours, the reaction being always alkaline towardsphenolphthaiein. The solution is then rendered feebly alkaline to litmuspaper. The reaction product has thefollowing constitution:

CZHB Gzlis CI13.(CHQMLYLCHLN-CflgnH.(CH2)3('"3 ,='-O CAHLILY-CHLCHZSOJNRInstead. of n-butyltaurine there may also be used another taurine; forinstance, isobutyltaurine, alpha-ethylhexyltaurine or anotheraminosulionic acid, for instance, sulfanilie acid or metanilic acid orethanol amine sulfuric acid ester.

(3) 33 parts of n -butyl-tetradecyl-carbamic acid chloride having theformula Cilia uHzo prepared from n-butyl-tetradecylamine and phosgeneare run into a solution of 13 parts ofsodium sarcosine in parts, ofwater at 70 C. to 80 C., while well stirring, the reaction being alwaysalkaline towards phenolphthalein and the whole is stirred until a testportion dissolves in dilute caustic soda solution to a clear solution.The reaction product has the following constitution:

cimmciimi i=0 cmr'tomcoomand may be used as washing agent.

(4) A mixture of carboxylic acids obtained by I the oxidation ofparaflin and containing carboxylic acids with 7 to 9 carbon atoms, istrans performed after the following scheme:

O-som R being aliphatic radicals having from 7 to 9 carbon atoms.

We claim:

1. The process of preparing capillary active compounds which comprisescausing compounds of the general formula wherein R and R1 stand foraliphatic hydrocarbonradicals containing at least 3 carbon atoms and Rand R1 together containing at least 11 carbon atoms, to react withphosgene and subsequently causing the condensation products to reactwith a member of the group consisting of aliphatic and aromatic aminocompounds substituted by a radical of the group consisting of SOaH,03031! and COOH.

formed b, way of the nitriles and hydrogenation of these nitriles into amixture of secondary amines, and then transformed into a mixture ofcarbamic acid chlorides by treatment with phosgene as described inExample 1. i 30 parts of this 2. The process of -preparing capillaryactive compounds which comprises causing compounds of the generalformula wherein R and R1 stand for aliphatic hydrocarbon radicalscontaining at least 3 carbon atoms and R and R1 together containing atleast 11 carbon atoms, to react with phosgene and subsequently causingthe condensation products to re act with an aliphatic amino sulionicacid.

3. The process of preparing capillary active' compounds which comprisesof the general formula R-III- R: H

causing compounds compounds which comprises causing compounds of thegeneral formula R-N-Rl wherein R and R1 stand for aliphatic hydrocarbonradicals containing,at least 3 carbon atoms and R and R1 togethercontaining at least 11 carbon atoms, to react with phosgene andsubsequently causing the condensation product to react with an aliphaticamino carboxylic acid.

5. As new compounds having capillary active properties the products ofthe general formula:

wherein R and R1 stand for aliphatic hydrocarbon radicals containing atleast 3 carbon atoms and R and R1 together containing at least 11 carbonatoms, R: stands for a member of the 10 group consisting of aliphaticand aromatic hydrocarbon radicals, R3 means a member of the groupconsisting of hydrogen and aliphatic hydrocarbon radicals and Y standsfor a member of the group consisting .of scan, OSOsI-I and 15 COOH. 6.Compounds as defined in claim 5, wherein Y stands for COOH.

'7. As a new capillary active compound C1His-NC7H 5 00 I cH,-1I-omom-so3rr 8. As a new capillary active compound om, c1115omxomncnommomcuromnom =0 cmqi rcmcmsoai LUDWIG ORTHNER.

HEINZ StiNKE.

